1,2-Dichloroethane → (S)-tert-butyl 1-(isoquinolin-7-ylamino)-4-methyl-1-oxopentan-2-yl(methyl)carbamate

HRID 1253854Notes

Reaction equation

HRID 1253854 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:17])[C@@H:9]([CH2:13][CH:14]([CH3:16])[CH3:15])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.[CH:22]1[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([NH2:32])[CH:30]=2)[CH:25]=[CH:24][N:23]=1>CN(C=O)C.CN(C1C=CN=CC=1)C>[CH:22]1[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([NH:32][C:10](=[O:12])[C@@H:9]([N:8]([CH3:17])[C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:13][CH:14]([CH3:16])[CH3:15])[CH:30]=2)[CH:25]=[CH:24][N:23]=1

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 7010555(2S)-2-{[(tert-butoxy)carbonyl](methyl)amino}-4-methylpentanoic acidHCID 14660277Isoquinolin-7-amine

Product 1

HCID 57788111(S)-tert-butyl 1-(isoquinolin-7-ylamino)-4-methyl-1-oxopentan-2-yl(methyl)carbamate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To (S)-2-(tert-butoxycarbonyl(methyl)amino)-4-methylpentanoic acid in DMF was added EDC, DMAP and isoquinolin-7-amine. This mixture was stirred for 4 hours and the reaction was washed with NaHCO3 (sat), extracted with EtOAc, dried (Na2SO4), filtered and evaporated. Column chromatography (SiO2, Hexanes/EtOAc) gave pure (S)-tert-butyl 1-(isoquinolin-7-ylamino)-4-methyl-1-oxopentan-2-yl(methyl)carbamate (E87).

Workup

  1. washthe reaction was washed with NaHCO3 (sat)
  2. extractionextracted with EtOAc
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-ac9c7f769c334ebc8db025a5410aae78
Source dataset
uspto-grants-2013_06
Patent number
US08455514B2

Reaction notes

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